3-bromo-2,6-dimethoxy-4-(methoxymethyl)phenol | 137898-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-bromo-2,6-dimethoxy-4-(methoxymethyl)phenol
• CAS: 137898-25-0
• 化学式: C₁₀H₁₃BrO₄
• 分子量: 277.115
• InChiKey: FNZFBFPYZNMAMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-2,6-dimethoxy-4-(methoxymethyl)phenol 在 bis-triphenylphosphine-palladium(II) chloride 2,4,6-三甲基吡啶 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-allyl-2,6-dimethoxy-4-(methoxymethyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes

  摘要：

  The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner. The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15%) of palladium are employed. On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the title substrates. However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents. Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction. Moreover, alkyl groups other than methyl cannot be introduced because beta-elimination occurs more rapidly. The potentially powerful synthesis of hindered biaryls has also been studied briefly. In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.

  DOI：

  10.1021/jo00028a051

文献信息

• Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes
  作者：Jose M. Saa、Gabriel Martorell、Angel Garcia-Raso

  DOI：10.1021/jo00028a051

  日期：1992.1

  The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner. The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15%) of palladium are employed. On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the title substrates. However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents. Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction. Moreover, alkyl groups other than methyl cannot be introduced because beta-elimination occurs more rapidly. The potentially powerful synthesis of hindered biaryls has also been studied briefly. In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.